Synthesis of diester-based biolubricants from epoxides

ABSTRACT

The present invention is generally directed to methods of making diester-based lubricant compositions, wherein formation of diester species proceeds via direct esterification of epoxide intermediates. In some embodiments, the methods for making such diester-based lubricants utilize a biomass precursor and/or low value (e.g., Fischer-Tropsch (FT) olefins and/or alcohols) so as to produce high value diester-based lubricants. In some embodiments, such diester-based lubricants are derived from FT olefins and fatty acids. The fatty acids can be from a bio-based source (i.e., biomass, renewable source) or can be derived from FT alcohols via oxidation.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application for patent is a Continuation of U.S. patent applicationSer. No. 12/023,695; filed Jan. 31, 2008.

FIELD OF THE INVENTION

This invention relates to methods of making ester-based lubricants, andspecifically to methods of synthesizing diester-basedlubricants—particularly wherein they are made from at least onebiologically-derived precursor.

BACKGROUND

Esters have been used as lubricating oils for over 50 years. They areused in a variety of applications ranging from jet engines torefrigeration. In fact, esters were the first synthetic crankcase motoroils in automotive applications. However, esters gave way topolyalphaolefins (PAOs) due to the lower cost of PAOs and theirformulation similarities to mineral oils. In fully synthetic motor oils,however, esters are almost always used in combination with PAOs tobalance the effect on seals, additive solubility, volatility reduction,and energy efficiency improvement by enhanced lubricity.

Ester-based lubricants, in general, have excellent lubricationproperties due to the polarity of the ester molecules of which they arecomprised. The polar ester groups of such molecules adhere topositively-charged metal surfaces creating protective films which slowdown the wear and tear of the metal surfaces. Such lubricants are lessvolatile than the traditional lubricants and tend to have much higherflash points and much lower vapor pressures. Ester lubricants areexcellent solvents and dispersants, and can readily solvate and dispersethe degradation by-products of oils. Therefore, they greatly reducesludge buildup. While ester lubricants are stable to thermal andoxidative processes, the ester functionalities give microbes a handlewith which to do their biodegrading more efficiently and moreeffectively than their mineral oil-based analogues—thereby renderingthem more environmentally-friendly. However, the preparation of estersis more involved and more costly than the preparation of their PAOcounterparts.

Recently, novel diester-based lubricant compositions and theircorresponding syntheses have been described in commonly-assigned U.S.patent application Ser. No. 11/673,879; filed Feb. 12, 2007. Thesynthetic routes described in this patent application comprise and/orgenerally proceed through the following sequence of reaction steps: (1)epoxidation of an olefin to form an epoxide; (2) conversion of theepoxide to form a diol; and (3) esterification of the diol to form adiester.

In view of the foregoing, and not withstanding such above-describedadvances in diester-based lubricant synthesis, a simpler, more efficientmethod of generating ester-based would be extremely useful—particularlywherein such methods utilize renewable raw materials in possiblecombination with the conversion of low value precursors (e.g.,Fischer-Tropsch olefins and/or alcohols) to high value ester lubricants.

BRIEF DESCRIPTION OF THE INVENTION

The present invention is generally directed to methods of makingdiester-based lubricant compositions. In some embodiments, the methodsfor making such diester-based lubricants utilize a biomass precursor. Inthese or other embodiments, lubricant precursor species can also besourced or otherwise derived from Fischer-Tropsch (FT) reaction productsand/or the pyrolysis of waste plastic.

In some embodiments, the present invention is directed to processescomprising the steps of (a) epoxidizing an olefin having a carbon numberof from R to 16 to form an epoxide comprising an epoxide ring; and (b)directly esterifying the epoxide with a C₂ to C₁₈ carboxylic acid toform a diester species having viscosity and pour point suitable for useas a lubricant. Such direct esterification generally proceeds withoutthe production and isolation of a diol intermediate that is subsequentlyesterified. Additionally, such epoxidizing and direct esterifying aretypically carried out on a plurality of olefins and epoxides,respectively.

Typically, the lubricant compositions produced by the above-mentionedprocess comprise a quantity of at least one diester species, the diesterspecies having the following structure:

wherein R₁, R₂, R₃, and R₄ are the same or independently selected fromC₂ to C₁₇ hydrocarbon groups.

The foregoing has outlined rather broadly the features of the presentinvention in order that the detailed description of the invention thatfollows may be better understood. Additional features and advantages ofthe invention will be described hereinafter which form the subject ofthe claims of the invention.

BRIEF DESCRIPTION OF THE DRAWINGS

For a more complete understanding of the present invention, and theadvantages thereof, reference is now made to the following descriptionstaken in conjunction with the accompanying drawings, in which:

FIG. 1 is a flow diagram illustrating a method of making diester-basedlubricant compositions, wherein the associated synthesis comprises adirect esterification of an epoxide intermediate—in accordance with someembodiments of the present invention;

FIG. 2 (Scheme 1) is a chemical flow diagram illustrating an exemplarymethod of making a diester-based lubricant composition without theproduction and isolation of a diol intermediate, in accordance with someembodiments of the present invention;

FIG. 3 depicts an exemplary mixture of species 1-7 that can be producedvia methods of the present invention;

FIG. 4 depicts an exemplary species 8, octanoic acid2-octanoyloxy-dodecyl ester, that can be produced via methods of thepresent invention;

FIG. 5 (Scheme 2); is a chemical flow diagram illustrating apreviously-presented (prior art) method for generating diester speciesoperable for use in lubricant compositions and is shown primarily forcomparative purposes; and

FIG. 6 depicts two diester-based compounds 9 and 10, prepared viamethods described previously and presented here primarily forcomparative purposes.

DETAILED DESCRIPTION OF THE INVENTION 1. Introduction

As mentioned in a preceding section, the present invention is directedto methods of making diester-based lubricant compositions. In someembodiments, such methods for making such diester-based lubricantsutilize a biomass precursor and/or low value olefins and/or alcohols(e.g., those derived from Fischer-Tropsch (FT) processes) so as toproduce high value diester-based lubricants. In some embodiments, suchdiester-based lubricants are derived from FT olefins and fatty(carboxylic) acids. In these or other embodiments, the fatty acids canbe from a bio-based source (i.e., biomass, renewable source) and/or canbe derived from FT alcohols via oxidation.

Because biolubricants and biofuels are increasingly capturing thepublic's attention and becoming topics of focus for many in the oilindustry, the use of biomass in the making of such above-mentionedlubricants could be attractive from several different perspectives. Tothe extent that biomass is so utilized in the making of thediester-hased lubricants of the present invention, such lubricants aredeemed to be biolubricants.

2. Definitions

“Lubricants,” as defined herein, are substances (usually a fluid underoperating conditions) introduced between two moving surfaces so toreduce the friction and wear between them. Base oils used as motor oilsare generally classified by the American Petroleum Institute as beingmineral oils (Group I, II, and III) or synthetic oils (Group IV and V).See American Petroleum Institute (API) Publication Number 1509.

“Pour point,” as defined herein, represents the lowest temperature atwhich a fluid will pour or flow. See, e.g., ASTM International StandardTest Methods D 5950-96, D 6892-03, and D 97.

“Cloud point,” as defined herein, represents the temperature at which afluid begins to phase separate due to crystal formation. See, e.g., ASTMStandard Test Methods D 5773-95, D 2500, D 5551, and D 5771.

“Centistoke,” abbreviated “cSt,” is a unit for kinematic viscosity of afluid (e.g., a lubricant), wherein 1 centistoke equals 1 millimetersquared per second (1 cSt=1 mm²/s). See, e.g., ASTM Standard Guide andTest Methods D 2270-04, D 445-06, D 6074, and D 2983.

With respect to describing molecules and/or molecular fragments herein,“Rn,” where “n” is an index, refers to a hydrocarbon group, wherein themolecules and/or molecular fragments can be linear and/or branched.

As defined herein, “C_(n),” where “n” is an integer, describes ahydrocarbon molecule or fragment (e.g., an alkyl group) wherein “n”denotes the number of carbon atoms in the fragment or molecule.

The prefix “bio,” as used herein, refers to an association with arenewable resource of biological origin, such resources generally beingexclusive of fossil fuels.

The term “internal olefin,” as used herein, refers to an olefin (i.e.,an alkene) having a non-terminal carbon-carbon double bond (C═C). Thisis in contrast to “α-olefins” which do bear a terminal carbon-carbondouble bond.

3. Diester Lubricant Compositions

Methods of the present invention generally provide for diester-basedlubricant compositions comprising a quantity of (vicinal) diesterspecies having the following chemical structure:

where R₁, R₂, R₃, and R₄ are the same or independently selected from aC₂ to C₁₇ carbon fragment.

Regarding the above-mentioned diester species, selection of R₁, R₂, R₃,and R₄ can follow any or all of several criteria. For example, in someembodiments, R₁, R₂, R₃, and R₄ are selected such that the kinematicviscosity of the composition at a temperature of 100° C. is typically 3centistokes (cSt) or greater. In some or other embodiments, R₁, R₂, R₃,and R₄ are selected such that the pour point of the resulting lubricantis −20° C. or lower. In some embodiments, R₁ and R₂ are selected to havea combined carbon number (i.e., total number of carbon atoms) of from 6to 14. In these or other embodiments, R₃ and R₄ are selected to have acombined carbon number of from 10 to 34. Depending on the embodiment,such resulting diester species can have a molecular mass between 340atomic mass units (a.m.u.) and 780 a.m.u.

In some embodiments, such above-described compositions are substantiallyhomogeneous in terms of their diester component. In some or otherembodiments, the diester component of such compositions comprises avariety (i.e., a mixture) of diester species. In some embodiments, thediester-based lubricant composition that is produced comprises at leastone diester species derived from a C₈ to C₁₄ olefin and a C₆ to C₁₄carboxylic acid.

In some of the above-described embodiments, the diester-based lubricantcomposition comprises diester species selected from the group consistingof decanoic acid 2-decanoyloxy-1-hexyl-octyl ester and its isomers,tetradecanoic acid-1-hexyl-2-tetradecanoyloxy-octyl esters and itsisomers, dodecanoic acid 2-dodecanoyloxy-1-hexyl-octyl ester and itsisomers, hexanoic acid 2-hexanoyloxy-1-hexy-octyl ester and its isomers,octanoic acid 2-octanoyloxy-1-hexyl-octyl ester and its isomers,_hexanoic acid 2-hexanoyloxy-1-pentyl-heptyl ester and isomers, octanoicacid 2-octanoyloxy-1-pentyl-heptyl ester and isomers, decanoic acid2-decanoyloxy-1-pentyl-heptyl ester and isomers, decanoicacid-2-cecanoyloxy-1-pentyl-heptyl ester and its isomers, dodecanoicacid-2-dodecanoyloxy-1-pentyl-heptyl ester and isomers, tetradecanoicacid 1-pentyl-2-tetradecanoyloxy-heptyl ester and isomers, tetradecanoicacid 1-butyl-2-tetradecanoyloxy-hexyl ester and isomers, dodecanoicacid-1-butyl-2-dodecanoyloxy-hexyl ester and isomers, decanoic acid1-butyl-2-decanoyloxy-hexyl ester and isomers, octanoic acid1-butyl-2-octanoyloxy-hexyl ester and isomers, hexanoic acid1-butyl-2-hexanoyloxy-hexyl ester and isomers, tetradecanoic acid1-propyl-2-tetradecanoyloxy-pentyl ester and isomers, dodecanoic acid2-dodecanoyloxy-1-propyl-pentyl ester and isomers, decanoic acid2-decanoyloxy-1-propyl-pentyl ester and isomers, octanoic acid2-octanoyloxy-1-propyl-pentyl ester and isomers, hexanoic acid2-hexanoyloxy-1-propyl-pentyl ester and isomers, and mixtures thereof.

It is worth noting that, in most applications, the above-describedesters and their compositions are unlikely to be used as lubricants bythemselves, but are usually used as blending stocks. As such, esterswith higher pour points may also be used as blending stocks with otherlubricant oils since they are very soluble in hydrocarbons andhydrocarbon-based oils.

4. Methods of Making Diester Lubricants

As mentioned above, the present invention is generally directed tomethods of making the above-described lubricant compositions.

Referring to the flow diagram shown in FIG. 1, in some embodimentsprocesses for making the above-mentioned (vicinal) diester species,typically having lubricating base oil viscosity and pour point, comprisethe following steps: (Step 101) epoxidizing an olefin (or quantity ofolefins) having a carbon number of from 8 to 16 to form an epoxidecomprising an epoxide ring; and (Step 102) directly esterifying(subjecting to esterification, i.e., diacylating) the epoxide with an C₂to C₁₈ carboxylic acid to form a diester species. Generally, lubricantcompositions comprising such diester species have a viscosity of 3centistokes or more at a temperature of 100° C. It will be appreciatedby those of skill in the art that, in the steps of epoxidizing andesterifying, a plurality of olefins and epoxides, respectively, aretypically so reacted, so as to effect the production of a plurality ofdiester species.

In some embodiments, where a quantity of such diester species is formed,the quantity of diester species can be substantially homogeneous, or itcan comprise a mixture of two or more different such diester species.

In some embodiments, the diester so formed is mixed or admixed with abase oil selected from the group consisting of Group I oils, Group IIoils, Group III oils, and mixtures thereof.

In some such above-described method embodiments, the olefin used is areaction product of a Fischer-Tropsch process. In some or otherembodiments, the olefin used is derived from the pyrolysis of wasteplastic. Generally speaking, however, the source of the olefin(s) is notparticularly limited.

In some embodiments, the olefin is an α-olefin (i.e., an olefin having adouble bond at a chain terminus). In such embodiments, it is oftennecessary to isomerize the olefin so as to internalize the double bond.Such isomerization is typically carried out catalytically using acatalyst such as, but not limited to, crystalline aluminosilicate andlike materials and aluminophosphates. See, e.g., U.S. Pat. Nos.2,537,283; 3,211,801; 3,270,085; 3,327,014; 3,304,343; 3,448,164;4,593,146; 3,723,564 and 6,281,404; the last of which claims acrystalline aluminophosphate-based catalyst with 1-dimensional pores ofsize between 3.8 Å and 5 Å.

As an example of such above-described isomerizing and as indicated inScheme 1 (FIG. 2), Fischer-Tropsch alpha olefins (α-olefins) can beisomerized to the corresponding internal olefins followed byepoxidation. The epoxides can then be transformed to the correspondingdiesters via direct (di)-esterification with the appropriate carboxylicacids. It is typically necessary to convert alpha olefins to internalolefins because diesters of alpha olefins, especially short chain alphaolefins, tend to be solids or waxes. “Internalizing” alpha olefinsfollowed by transformation to the diester functionalities introducesbranching along the chain which reduces the pour point of the intendedproducts. The ester groups with their polar character would furtherenhance the viscosity of the final product. Adding branches during theisomerizing (isomerization) step will tend to increase carbon number andhence viscosity. It can also decrease the associated pour and cloudpoints. It is typically preferable to have a few longer branches thanmany short branches, since increased branching tends to lower theviscosity index (VI)

Regarding the step of epoxidizing (i.e., the epoxidation step), in someembodiments, the above-described olefin (preferably an internal olefin)can be reacted with a peroxide (e.g., H₂O₂) or a peroxy acid (e.g.,peroxyacetic acid) to generate an epoxide. See, e.g., D. Swern, inOrganic Peroxides Vol. II, Wiley-Interscience, New York, 1971, pp.355-533; and B. Plesnicar, in Oxidation in Organic Chemistry, Part C, W.Trahanovsky (ed.), Academic Press, New York 1978, pp. 221-253.

Regarding the step of directly esterifying (i.e., the esterificationstep), in some embodiments this step is carried out in the presence of acatalyst. Such catalyst species can include, but are not limited to,H₃PO₄, H₂SO₄, sulfonic acid, Lewis acids, silica and alumina-based solidacids, amberlyst, tungsten oxide, and mixtures and combinations thereof,and the like.

In some such above-described method embodiments, the carboxylic acid canbe derived from alcohols generated by a Fischer-Tropsch process and/orit can be a bio-derived fatty acid. Note that the carboxylic acids canbe of a single type (e.g., length), or they can be a mixture of types.Additionally, in some embodiments, quantities of carboxylic acidanhydride can also be utilized together with the carboxylic acid in theesterification.

In some embodiments, during the step of directly esterifying, effortsare made to remove water produced as a result of the esterifyingprocess. Such efforts can positively impact the diester yield.

Regardless of the source of the olefin, in some embodiments, thecarboxylic acid used in the above-described method is derived frombiomass. In some such embodiments, this involves the extraction of someoil (e.g., triglyceride) component from the biomass and hydrolysis ofthe triglycerides of which the oil component is comprised so as to formfree carboxylic acids.

5. Variations

Variations (i.e., alternate embodiments) on the above-describedlubricant compositions include, but are not limited to, utilizingmixtures of isomeric olefins and or mixtures of olefins having adifferent number of carbons. This leads to diester mixtures in theproduct compositions. Variations on the above-described processesfurther include, but are not limited to, using carboxylic acids derivedfrom FT alcohols by oxidation.

The advantages of the methods of the present invention notwithstanding,in some embodiments, it may be advantageous to combine the methods ofthe present invention with those described in commonly-assigned U.S.patent application Ser. No. 11/673,879, filed Feb. 12, 2007 andincorporated by reference herein.

6. Examples

The following examples are provided to demonstrate, and/or more fullyillustrate, particular embodiments of the present invention. It shouldbe appreciated by those of skill in the art that the methods disclosedin the examples which follow merely represent exemplary embodiments ofthe present invention. However, those of skill in the art should, inlight of the present disclosure, appreciate that many changes can bemade in the specific embodiments described and still obtain a like orsimilar result without departing from the spirit and scope of thepresent invention.

Example 1

This Example serves to illustrate the epoxidation of tetradecenes toform tetradecene epoxides, and the subsequent esterification of thetetradecene epoxides to form diester species operable for use in/asdiester-based lubricant compositions, in accordance with someembodiments of the present invention.

Tetradecenes were epoxidized as follows using a general procedure forthe epoxidation of 7,8-tetradecene. To a stirred solution of 143 grams(0.64 mole) of 77% mCPBA (meta-chloroperoxybenzoic acid) in 500 mLchloroform, 100 grams (0.51 mol) of 7,8-tetradecene in 200 mL chloroformwas added drop-wise over a 45-minute period. The resulting reactionmixture was stirred overnight. The resulting milky solution wassubsequently filtered to remove meta-chloro-benzoic acid that formedtherein. The filtrate was then washed with a 10% aqueous solution ofsodium bicarbonate. The organic layer was dried over anhydrous magnesiumsulfate and concentrated on a rotary evaporator. The reaction affordedthe desired epoxide (isomers of n-tetradecene epoxides) as colorless oilin 93% yield.

The isomers of n-tetradecene epoxides (10.6 grams, 50 mmol) were mixedwith lauric acid (30 grams, 150 mmol) and 85% H₃PO₄ (0.1 grams, 0.87mmol). The mixture was stirred and bubbled/purged with nitrogen at 150°C. for 20 hours. Excess lauric acid was removed from the product firstby recrystallization in hexane with subsequent filtration at −15° C.,and then by adding a calculated amount of 1N NaOH solution and filteringout the sodium laurate salt. The diester product collected (21.8 grams,73% yield) was a light yellow, transparent oil. The oil comprised amixture of the diester species 1-7 depicted in FIG. 3.

Example 2

This Example serves to illustrate the direct esterification of1-dodecene epoxide (2-decyl-oxirane) to yield a diester species, inaccordance with some embodiments of the present invention.

Quantities of 1-dodecene epoxide (9.2 grams, 50 mmol) and octanoic acid(14.4 grams, 100 mmol) were dissolved in 12 mL toluene, and 85% H₃PO₄(0.3 grams, 0.87 mmol) was added. The mixture was stirred andbubbled/purged with nitrogen at 140° C. for 23 hours. The mixture wassubsequently washed with a K₂CO₃-saturated solution, filtered andseparated to remove the acids, the organic layer was dried by anhydrousMgSO₄ and evaporated under reduced pressure. Referring to FIG. 4, thediester product 8, octanoic acid 2-octanoyloxy-dodecyl ester, (18 grams,83% yield) was a transparent, colorless oil.

Example 3 (Comparative)

This Example serves to illustrate synthesis and isolation of a diol, andsubsequent esterification of said diol, en route to synthesis of adiester species, in accordance with the methods described incommonly-assigned U.S. patent application Ser. No. 11/673,879, filedFeb. 12, 2007 and incorporated by reference herein. This comparativeExample differs from embodiments of the present invention in that a diolis produced and isolated for subsequent esterification (as depicted inFIG. 5, Scheme 2), instead of esterifying the epoxide directly.

1. Diol Preparation and Isolation

In a 3-neck 1 mL reaction flask equipped with an overhead stirrer and anice bath, 75 mL of 30% hydrogen peroxide were added to 300 mL of 96%formic acid. To this mixture, 100 grams (0.51 mole) of 7-tetradecene(purchased from Aldrich Chemical Co.) was added slowly over a 30 minuteperiod via a dropping funnel. Once the addition of the olefin wascomplete, the reaction was allowed to stir while cooling with theice-bath to prevent rise in the temperature above 40-50° C. for 2 hrs.The ice-bath was then removed and the reaction was stirred at roomtemperature overnight. The reaction mixture was concentrated with arotary evaporator in a hot water bath at ˜30 torr to remove most of thewater and formic acid. Then, 100 mL of ice-cold 1 M solution of sodiumhydroxide was added very slowly (in small portions) and carefully to theremaining residue of the reaction. Once all the sodium hydroxidesolution was added, the mixture was allowed to stir for an additional45-60 minutes at room temperature. The mixture was diluted with 500 mLethyl acetate and transferred to a reparatory funnel. The organic layerwas sequestered and the aqueous layer was extracted 3 times (3×200 mL)with ethyl acetate. The ethyl acetate extracts were combined and driedover anhydrous MgSO₄. Filtration, followed by concentration on a rotaryevaporator at reduced pressure in a hot water bath gave the desired diolas white powder in 88% yield (95 grams). The produced and isolated diol(tetradecane-7,8-diol) was characterized by nuclear magnetic resonance(NMR) spectroscopy and gas-chromatography/mass spectrometry (GC/MS).

2. Conversion of the Diol to a Diester

What follows serves to illustrate synthesis of diester 10 (decanoic acid2-decanoyloxy-1-hexyl-octyl ester) from tetradecane-7,8-diol (seeabove). FIG. 6 depicts diester 10, as well as diester 9 (hexanoic acid2-hexanoyloxy-1-hexyl-octyl ester), the latter being similarly preparedby using hexanoic acid or an anhydrous variant thereof.

In a 3-neck 1 L reaction flask equipped with an overhead stirrer, refluxcondenser and a dropping funnel, 50 grams (0.23 mol) oftetradecane-7,8-diol (prepared above) and 60 grams (0.59 mol)triethylamine and a catalytic amount of dimethylaminopyridine (6.5grams; 0.052 mol)) were mixed in 500 mL anhydrous hexane. The solutionwas cooled down with an ice bath. To this solution 97 grams (0.51 mol)decanoyl chloride was added drop-wise over a 15 minute period. Once theaddition was complete, the ice bath was removed and the reaction wasallowed to stir overnight. Then, an additional 12 grams of the decanoylchloride was added and the reaction was refluxed overnight. Theresulting “milky” reaction solution was neutralized with water. Theresulting two layer mixture was then transferred to a separatory funnel.The organic (top) layer was separated and washed with 2×500 mL water.The aqueous layer was extracted with 3×300 mL ether. The ether extractsand the original organic layer were combined, dried over MgSO₄,filtered, and concentrated over a rotary evaporator at reduced pressure.The resulting residue was analyzed by NMR and infrared (IR)spectroscopies and GC/MS. Such analysis confirmed the presence ofdecanoic acid. The mixture was treated with 3 M aqueous solution ofsodium carbonate (to neutralize the acid impurity) in 500 mL hexane. Thehexane layer was dried over MgSO₄, filtered and concentrated on a rotaryevaporator to give the desired diester product as a colorless viscousoil with a sweet odor in 81% yield (100.5 grams). GC/MS indicated thepresence of less than 1% residual acid in the product.

7. Summary

In summary, the present invention provides for methods (processes) ofmaking diester-based lubricant compositions, wherein such methodsgenerally comprise a step of directly diesterifying an epoxideintermediate. In some embodiments, the methods for making suchdiester-based lubricants utilize a biomass precursor and/or low valueFischer-Tropsch olefins and/or alcohols so as to produce high valuediester-based lubricants. In some embodiments, such diester-basedlubricants are derived from FT olefins and fatty acids. The fatty acidscan be from a bio-based source (i.e., biomass, renewable source) or canbe derived from FT alcohols via oxidation.

All patents and publications referenced herein are hereby incorporatedby reference to the extent not inconsistent herewith. It will beunderstood that certain of the above-described structures, functions,and operations of the above-described embodiments are not necessary topractice the present invention and are included in the descriptionsimply for completeness of an exemplary embodiment or embodiments. Inaddition, it will be understood that specific structures, functions, andoperations set forth in the above-described referenced patents andpublications can be practiced in conjunction with the present invention,but they are not essential to its practice. It is therefore to beunderstood that the invention may be practiced otherwise than asspecifically described without actually departing from the spirit andscope of the present invention as defined by the appended claims.

1. A process comprising: a) epoxidizing an olefin having a carbon numberof from 6 to 36 to form an epoxide having an epoxide ring, wherein theolefin is first double bond isomerized from an α-olefin to an internalolefin using an olefin isomerization catalyst; and b) directlyesterifying the epoxide with a C₂ to C₁₈ carboxylic acid to form adiester species having viscosity and pour point suitable for use as alubricant or component thereof.
 2. The process of claim 1, wherein thestep of directly esterifying is catalyzed by the presence of a catalyst.3. The process of claim 2, wherein the catalyst is an acid catalystselected from the group consisting of H₃PO₄, H₂SO₄, sulfonic acid, Lewisacids, silica and alumina-based solid acids, amberlyst, tungsten oxide,and combinations thereof.
 4. The process of claim 1, wherein the step ofdirectly esterifying additionally comprises the presence of a carboxylicacid anhydride.
 5. The process of claim 1, further comprising a step ofblending the diester species with one or more other species selectedfrom the group consisting of other diester species, Group I oils, GroupII oils, Group III oils, and mixtures thereof.
 6. The process of claim1, wherein the olefin is derived from a Fischer-Tropsch process or frompyrolysis of waste plastic.
 7. The process of claim 1, wherein thecarboxylic acid is derived from biomass via extraction and subsequenthydrolysis of triglycerides.
 8. The process of claim 1, wherein thediester species formed is selected from the group consisting of decanoicacid 2-decanoyloxy-1-hexyl-octyl ester and its isomers, tetradecanoicacid-1-hexyl-2-tetradecanoyloxy-octyl esters and its isomers, dodecanoicacid 2-dodecanoyloxy-1-hexyl-octyl ester and its isomers, hexanoic acid2-hexanoyloxy-1-hexy-octyl ester and its isomers, octanoic acid2-octanoyloxy-1-hexyl-octyl ester and its isomers, hexanoic acid2-hexanoyloxy-1-pentyl-heptyl ester and isomers, octanoic acid2-octanoyloxy-1-pentyl-heptyl ester and isomers, decanoic acid2-decanoyloxy-1-pentyl-heptyl ester and isomers, decanoicacid-2-cecanoyloxy-1-pentyl-heptyl ester and its isomers, dodecanoicacid-2-dodecanoyloxy-1-pentyl-heptyl ester and isomers, tetradecanoicacid 1-pentyl-2-tetradecanoyloxy-heptyl ester and isomers, tetradecanoicacid 1-butyl-2-tetradecanoyloxy-hexyl ester and isomers, dodecanoicacid-1-butyl-2-dodecanoyloxy-hexyl ester and isomers, decanoic acid1-butyl-2-decanoyloxy-hexyl ester and isomers, octanoic acid1-butyl-2-octanoyloxy-hexyl ester and isomers, hexanoic acid1-butyl-2-hexanoyloxy-hexyl ester and isomers, tetradecanoic acid1-propyl-2-tetradecanoyloxy-pentyl ester and isomers, dodecanoic acid2-dodecanoyloxy-1-propyl-pentyl ester and isomers, decanoic acid2-decanoyloxy-1-propyl-pentyl ester and isomers, octanoic acid2-octanoyloxy-1-propyl-pentyl ester and isomers, hexanoic acid2-hexanoyloxy-1-propyl-pentyl ester and isomers, and mixtures thereof.9. A process comprising: a) epoxidizing an olefin having a carbon numberof from 6 to 36 to form an epoxide having an epoxide ring, wherein theolefin is first double bond isomerized from an α-olefin to an internalolefin in the presence of an olefin isomerization catalyst; and b)esterifying the epoxide with a C₂ to C₁₈ carboxylic acid, without firstproducing and isolating an intermediate diol species, so as to form adiester species having viscosity and pour point suitable for use as alubricant or component thereof, wherein the step of esterifying iscatalyzed by the presence of a catalyst.
 10. The process of claim 9,wherein the catalyst is an acid selected from the group consisting ofH₃PO₄, H₂SO₄, sulfonic acid, Lewis acids, silica and alumina-based solidacids, amberlyst, tungsten oxide, and combinations thereof.
 11. Theprocess of claim 9, wherein the step of esterifying additionallycomprises the presence of a carboxylic acid anhydride.
 12. The processof claim 9, wherein the olefin is derived from a Fischer-Tropschreaction process or via pyrolysis of waste plastic.
 13. The process ofclaim 9, wherein the carboxylic acid is derived from biomass viaextraction and subsequent hydrolysis of triglycerides.
 14. The processof claim 9, wherein the diester species formed is selected from thegroup consisting of decanoic acid 2-decanoyloxy-1-hexyl-octyl ester andits isomers, tetradecanoic acid-1-hexyl-2-tetradecanoyloxy-octyl estersand its isomers, dodecanoic acid 2-dodecanoyloxy-1-hexyl-octyl ester andits isomers, hexanoic acid 2-hexanoyloxy-1-hexy-octyl ester and itsisomers, octanoic acid 2-octanoyloxy-1-hexyl-octyl ester and itsisomers, hexanoic acid 2-hexanoyloxy-1-pentyl-heptyl ester and isomers,octanoic acid 2-octanoyloxy-1-pentyl-heptyl ester and isomers, decanoicacid 2-decanoyloxy-1-pentyl-heptyl ester and isomers, decanoicacid-2-cecanoyloxy-1-pentyl-heptyl ester and its isomers, dodecanoicacid-2-dodecanoyloxy-1-pentyl-heptyl ester and isomers, tetradecanoicacid 1-pentyl-2-tetradecanoyloxy-heptyl ester and isomers, tetradecanoicacid 1-butyl-2-tetradecanoyloxy-hexyl ester and isomers, dodecanoicacid-1-butyl-2-dodecanoyloxy-hexyl ester and isomers, decanoic acid1-butyl-2-decanoyloxy-hexyl ester and isomers, octanoic acid1-butyl-2-octanoyloxy-hexyl ester and isomers, hexanoic acid1-butyl-2-hexanoyloxy-hexyl ester and isomers, tetradecanoic acid1-propyl-2-tetradecanoyloxy-pentyl ester and isomers, dodecanoic acid2-dodecanoyloxy-1-propyl-pentyl ester and isomers, decanoic acid2-decanoyloxy-1-propyl-pentyl ester and isomers, octanoic acid2-octanoyloxy-1-propyl-pentyl ester and isomers, hexanoic acid2-hexanoyloxy-1-propyl-pentyl ester and isomers, and mixtures thereof.15. A process comprising: a) epoxidizing a plurality of olefins, saidolefins having a carbon number of from 6 to 36, to form a plurality ofepoxides, each of which has an epoxide ring, wherein the olefin is firstdoubled bond isomerized from an α-olefin to an internal olefin using anolefin isomerization catalyst; and b) esterifying the epoxides with aplurality of C₂ to C₁₈ carboxylic acids, converting less than 10 percentof said epoxides to diols, so as to form a diester composition having aviscosity and pour point suitable for use as a lubricant or componentthereof.
 16. The process of claim 15, wherein the step of esterifying iscatalyzed by the presence of a acid catalyst.
 17. The process of claim15, wherein the step of esterifying additionally comprises the presenceof a carboxylic acid anhydride.
 18. The process of claim 15, wherein atleast some of the plurality of olefins are derived, as a reactionproduct, from a pre-process selected from the group consisting ofFischer-Tropsch synthesis, pyrolysis of waste plastic, and combinationsthereof.
 19. The process of claim 15, wherein at least some of thecarboxylic acids are derived from biomass via extraction and subsequenthydrolysis of triglycerides.
 20. The process of claim 15, wherein thediester composition formed comprises diester species selected from thegroup consisting of decanoic acid 2-decanoyloxy-1-hexyl-octyl ester andits isomers, tetradecanoic acid-1-hexyl-2-tetradecanoyloxy-octyl estersand its isomers, dodecanoic acid 2-dodecanoyloxy-1-hexyl-octyl ester andits isomers, hexanoic acid 2-hexanoyloxy-1-hexy-octyl ester and itsisomers, octanoic acid 2-octanoyloxy-1-hexyl-octyl ester and itsisomers, hexanoic acid 2-hexanoyloxy-1-pentyl-heptyl ester and isomers,octanoic acid 2-octanoyloxy-1-pentyl-heptyl ester and isomers, decanoicacid 2-decanoyloxy-1-pentyl-heptyl ester and isomers, decanoicacid-2-cecanoyloxy-1-pentyl-heptyl ester and its isomers, dodecanoicacid-2-dodecanoyloxy-1-pentyl-heptyl ester and isomers, tetradecanoicacid 1-pentyl-2-tetradecanoyloxy-heptyl ester and isomers, tetradecanoicacid 1-butyl-2-tetradecanoyloxy-hexyl ester and isomers, dodecanoicacid-1-butyl-2-dodecanoyloxy-hexyl ester and isomers, decanoic acid1-butyl-2-decanoyloxy-hexyl ester and isomers, octanoic acid1-butyl-2-octanoyloxy-hexyl ester and isomers, hexanoic acid1-butyl-2-hexanoyloxy-hexyl ester and isomers, tetradecanoic acid1-propyl-2-tetradecanoyloxy-pentyl ester and isomers, dodecanoic acid2-dodecanoyloxy-1-propyl-pentyl ester and isomers, decanoic acid2-decanoyloxy-1-propyl-pentyl ester and isomers, octanoic acid2-octanoyloxy-1-propyl-pentyl ester and isomers, hexanoic acid2-hexanoyloxy-1-propyl-pentyl ester and isomers, and mixtures thereof.